Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015263
Secondary Accession Numbers
  • HMDB15263
Metabolite Identification
Common NameProguanil
DescriptionProguanil, also known as chloroguanide, belongs to the class of organic compounds known as 1-arylbiguanides. These are organonitrogen compounds containing a biguanide that is N-arylsubstituted at only the 1-position. Proguanil is a drug which is used for the causal prevention and suppression of malaria caused by susceptible strains of p. falciparum and other species of plasmodium found in some geographical areas of the world. Proguanil is a very strong basic compound (based on its pKa).
Structure
Data?1582753277
Synonyms
ValueSource
1-(p-Chlorophenyl)-5-isopropylbiguanideChEBI
ChlorguanideChEBI
ChloroguanideChEBI
N-(4-Chlorophenyl)-n'-(isopropyl)-imidodicarbonimidic diamideChEBI
ProguanilumChEBI
Chemical FormulaC11H16ClN5
Average Molecular Weight253.731
Monoisotopic Molecular Weight253.109423244
IUPAC Name(E)-1-({amino[(4-chlorophenyl)amino]methylidene}amino)-N'-(propan-2-yl)methenimidamide
Traditional Nameproguanil
CAS Registry Number500-92-5
SMILES
CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
InChI KeySSOLNOMRVKKSON-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-arylbiguanides. These are organonitrogen compounds containing a biguanide that is N-arylsubstituted at only the 1-position.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct Parent1-arylbiguanides
Alternative Parents
Substituents
  • 1-arylbiguanide
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.29 g/LNot Available
LogP1.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM161.330932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP1.9ALOGPS
logP1.89ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)19.77ChemAxon
pKa (Strongest Basic)10.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.07 m³·mol⁻¹ChemAxon
Polarizability26.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+169.48630932474
DeepCCS[M-H]-167.12930932474
DeepCCS[M-2H]-200.01530932474
DeepCCS[M+Na]+175.5830932474
AllCCS[M+H]+156.832859911
AllCCS[M+H-H2O]+153.332859911
AllCCS[M+NH4]+159.932859911
AllCCS[M+Na]+160.832859911
AllCCS[M-H]-158.732859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-160.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProguanilCC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C13332.8Standard polar33892256
ProguanilCC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C11954.4Standard non polar33892256
ProguanilCC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C12452.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Proguanil,1TMS,isomer #1CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C2418.1Semi standard non polar33892256
Proguanil,1TMS,isomer #1CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C2178.3Standard non polar33892256
Proguanil,1TMS,isomer #1CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C4055.1Standard polar33892256
Proguanil,1TMS,isomer #2CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C2431.9Semi standard non polar33892256
Proguanil,1TMS,isomer #2CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C2140.7Standard non polar33892256
Proguanil,1TMS,isomer #2CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C4092.3Standard polar33892256
Proguanil,1TMS,isomer #3CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C2248.3Semi standard non polar33892256
Proguanil,1TMS,isomer #3CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C2143.4Standard non polar33892256
Proguanil,1TMS,isomer #3CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C4083.9Standard polar33892256
Proguanil,2TMS,isomer #1CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N[Si](C)(C)C2482.5Semi standard non polar33892256
Proguanil,2TMS,isomer #1CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N[Si](C)(C)C2096.2Standard non polar33892256
Proguanil,2TMS,isomer #1CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N[Si](C)(C)C3758.8Standard polar33892256
Proguanil,2TMS,isomer #2CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C2312.1Semi standard non polar33892256
Proguanil,2TMS,isomer #2CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C2189.0Standard non polar33892256
Proguanil,2TMS,isomer #2CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C3750.2Standard polar33892256
Proguanil,2TMS,isomer #3CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C2422.1Semi standard non polar33892256
Proguanil,2TMS,isomer #3CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C2217.8Standard non polar33892256
Proguanil,2TMS,isomer #3CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C3802.8Standard polar33892256
Proguanil,2TMS,isomer #4CC(C)/N=C(\N)N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C2294.4Semi standard non polar33892256
Proguanil,2TMS,isomer #4CC(C)/N=C(\N)N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C2126.5Standard non polar33892256
Proguanil,2TMS,isomer #4CC(C)/N=C(\N)N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C3786.2Standard polar33892256
Proguanil,2TMS,isomer #5CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C2429.6Semi standard non polar33892256
Proguanil,2TMS,isomer #5CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C2201.5Standard non polar33892256
Proguanil,2TMS,isomer #5CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C3926.7Standard polar33892256
Proguanil,3TMS,isomer #1CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C2347.6Semi standard non polar33892256
Proguanil,3TMS,isomer #1CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C2181.4Standard non polar33892256
Proguanil,3TMS,isomer #1CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C3346.5Standard polar33892256
Proguanil,3TMS,isomer #2CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2469.1Semi standard non polar33892256
Proguanil,3TMS,isomer #2CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2123.3Standard non polar33892256
Proguanil,3TMS,isomer #2CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C3495.2Standard polar33892256
Proguanil,3TMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2531.6Semi standard non polar33892256
Proguanil,3TMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2128.0Standard non polar33892256
Proguanil,3TMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3385.9Standard polar33892256
Proguanil,3TMS,isomer #4CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2368.5Semi standard non polar33892256
Proguanil,3TMS,isomer #4CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2274.0Standard non polar33892256
Proguanil,3TMS,isomer #4CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3528.4Standard polar33892256
Proguanil,3TMS,isomer #5CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2286.5Semi standard non polar33892256
Proguanil,3TMS,isomer #5CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2318.8Standard non polar33892256
Proguanil,3TMS,isomer #5CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3650.6Standard polar33892256
Proguanil,4TMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2390.7Semi standard non polar33892256
Proguanil,4TMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2301.9Standard non polar33892256
Proguanil,4TMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C3097.4Standard polar33892256
Proguanil,4TMS,isomer #2CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2441.4Semi standard non polar33892256
Proguanil,4TMS,isomer #2CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2269.7Standard non polar33892256
Proguanil,4TMS,isomer #2CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3010.7Standard polar33892256
Proguanil,4TMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2550.3Semi standard non polar33892256
Proguanil,4TMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2176.6Standard non polar33892256
Proguanil,4TMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3162.5Standard polar33892256
Proguanil,5TMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2529.6Semi standard non polar33892256
Proguanil,5TMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2378.3Standard non polar33892256
Proguanil,5TMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2817.3Standard polar33892256
Proguanil,1TBDMS,isomer #1CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C2576.9Semi standard non polar33892256
Proguanil,1TBDMS,isomer #1CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C2316.4Standard non polar33892256
Proguanil,1TBDMS,isomer #1CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C4032.5Standard polar33892256
Proguanil,1TBDMS,isomer #2CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C2621.8Semi standard non polar33892256
Proguanil,1TBDMS,isomer #2CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C2275.3Standard non polar33892256
Proguanil,1TBDMS,isomer #2CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C4063.8Standard polar33892256
Proguanil,1TBDMS,isomer #3CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2422.3Semi standard non polar33892256
Proguanil,1TBDMS,isomer #3CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2357.0Standard non polar33892256
Proguanil,1TBDMS,isomer #3CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C4116.6Standard polar33892256
Proguanil,2TBDMS,isomer #1CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2860.7Semi standard non polar33892256
Proguanil,2TBDMS,isomer #1CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2422.7Standard non polar33892256
Proguanil,2TBDMS,isomer #1CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3659.5Standard polar33892256
Proguanil,2TBDMS,isomer #2CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2698.6Semi standard non polar33892256
Proguanil,2TBDMS,isomer #2CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2535.3Standard non polar33892256
Proguanil,2TBDMS,isomer #2CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3740.4Standard polar33892256
Proguanil,2TBDMS,isomer #3CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2780.3Semi standard non polar33892256
Proguanil,2TBDMS,isomer #3CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2552.1Standard non polar33892256
Proguanil,2TBDMS,isomer #3CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3764.3Standard polar33892256
Proguanil,2TBDMS,isomer #4CC(C)/N=C(\N)N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2683.6Semi standard non polar33892256
Proguanil,2TBDMS,isomer #4CC(C)/N=C(\N)N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2536.9Standard non polar33892256
Proguanil,2TBDMS,isomer #4CC(C)/N=C(\N)N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3807.7Standard polar33892256
Proguanil,2TBDMS,isomer #5CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2790.8Semi standard non polar33892256
Proguanil,2TBDMS,isomer #5CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2589.8Standard non polar33892256
Proguanil,2TBDMS,isomer #5CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3897.1Standard polar33892256
Proguanil,3TBDMS,isomer #1CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2947.6Semi standard non polar33892256
Proguanil,3TBDMS,isomer #1CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2653.4Standard non polar33892256
Proguanil,3TBDMS,isomer #1CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3382.1Standard polar33892256
Proguanil,3TBDMS,isomer #2CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3064.2Semi standard non polar33892256
Proguanil,3TBDMS,isomer #2CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2712.2Standard non polar33892256
Proguanil,3TBDMS,isomer #2CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3480.2Standard polar33892256
Proguanil,3TBDMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3086.2Semi standard non polar33892256
Proguanil,3TBDMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2679.1Standard non polar33892256
Proguanil,3TBDMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3382.3Standard polar33892256
Proguanil,3TBDMS,isomer #4CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2958.2Semi standard non polar33892256
Proguanil,3TBDMS,isomer #4CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2735.9Standard non polar33892256
Proguanil,3TBDMS,isomer #4CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3594.6Standard polar33892256
Proguanil,3TBDMS,isomer #5CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2962.0Semi standard non polar33892256
Proguanil,3TBDMS,isomer #5CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2827.1Standard non polar33892256
Proguanil,3TBDMS,isomer #5CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3716.4Standard polar33892256
Proguanil,4TBDMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3234.1Semi standard non polar33892256
Proguanil,4TBDMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2961.6Standard non polar33892256
Proguanil,4TBDMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3277.3Standard polar33892256
Proguanil,4TBDMS,isomer #2CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3202.8Semi standard non polar33892256
Proguanil,4TBDMS,isomer #2CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2918.0Standard non polar33892256
Proguanil,4TBDMS,isomer #2CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3213.8Standard polar33892256
Proguanil,4TBDMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3321.0Semi standard non polar33892256
Proguanil,4TBDMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2964.8Standard non polar33892256
Proguanil,4TBDMS,isomer #3CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3287.5Standard polar33892256
Proguanil,5TBDMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3502.7Semi standard non polar33892256
Proguanil,5TBDMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3242.3Standard non polar33892256
Proguanil,5TBDMS,isomer #1CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3123.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Proguanil GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9820000000-cb5312c89efbffe9e2582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Proguanil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Proguanil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 10V, Positive-QTOFsplash10-0udi-0690000000-77111e4056e6fd55dd002016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 20V, Positive-QTOFsplash10-0h90-2920000000-d8728ebf8c07ca389fa52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 40V, Positive-QTOFsplash10-0h93-7900000000-fd5b681d853f5a600e4e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 10V, Negative-QTOFsplash10-0udi-4890000000-9cd845da8e9126cab5cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 20V, Negative-QTOFsplash10-0kdi-5930000000-180eb772ddf87acf88392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 40V, Negative-QTOFsplash10-056u-9700000000-782e67963a33097714792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 10V, Positive-QTOFsplash10-0udi-0490000000-68ae471c348c1e55ed832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 20V, Positive-QTOFsplash10-0fka-2910000000-8cebe23f69e7fa7655c22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 40V, Positive-QTOFsplash10-0fb9-4900000000-2b8c7a01743760b29b3e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 10V, Negative-QTOFsplash10-0f8d-4900000000-3f8bd7947322c308f7102021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 20V, Negative-QTOFsplash10-0ue9-5900000000-ca547f95f87c9d9ebe7a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proguanil 40V, Negative-QTOFsplash10-001i-9200000000-81212b3c9362bcd2da622021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01131 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01131 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01131
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4754
KEGG Compound IDC07631
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProguanil
METLIN IDNot Available
PubChem Compound4923
PDB IDNot Available
ChEBI ID8455
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in dihydrofolate reductase activity
Specific function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:
DHFR
Uniprot ID:
P00374
Molecular weight:
21452.61
References
  1. Kaneko A, Bergqvist Y, Takechi M, Kalkoa M, Kaneko O, Kobayakawa T, Ishizaki T, Bjorkman A: Intrinsic efficacy of proguanil against falciparum and vivax malaria independent of the metabolite cycloguanil. J Infect Dis. 1999 Apr;179(4):974-9. [PubMed:10068594 ]
  2. Vasconcelos KF, Plowe CV, Fontes CJ, Kyle D, Wirth DF, Pereira da Silva LH, Zalis MG: Mutations in Plasmodium falciparum dihydrofolate reductase and dihydropteroate synthase of isolates from the Amazon region of Brazil. Mem Inst Oswaldo Cruz. 2000 Sep-Oct;95(5):721-8. [PubMed:10998224 ]
  3. Tahar R, de Pecoulas PE, Basco LK, Chiadmi M, Mazabraud A: Kinetic properties of dihydrofolate reductase from wild-type and mutant Plasmodium vivax expressed in Escherichia coli. Mol Biochem Parasitol. 2001 Apr 6;113(2):241-9. [PubMed:11295178 ]
  4. Durand R, Jafari S, Bouchaud O, Ralaimazava P, Keundjian A, Le Bras J: Plasmodium falciparum: pfcrt and DHFR mutations are associated with failure of chloroquine plus proguanil prophylaxis in travelers. J Infect Dis. 2001 Dec 15;184(12):1633-4. [PubMed:11740746 ]
  5. Le Bras J, Durand R: The mechanisms of resistance to antimalarial drugs in Plasmodium falciparum. Fundam Clin Pharmacol. 2003 Apr;17(2):147-53. [PubMed:12667224 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Lu AH, Shu Y, Huang SL, Wang W, Ou-Yang DS, Zhou HH: In vitro proguanil activation to cycloguanil is mediated by CYP2C19 and CYP3A4 in adult Chinese liver microsomes. Acta Pharmacol Sin. 2000 Aug;21(8):747-52. [PubMed:11501186 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]